She was assuring me—an inexperienced, somewhat terrified newbie in a worldwide marketing department—that I was equipped for the job. She hired me because I was a good writer, not because I knew anything about business, or strategy, or business strategy. Other people had that expertise. I didn’t need it.

What I needed was questions—and the curiosity and courage to ask them.

Good communicators ask good questions.

Twenty-some years later, I am no newbie. But I still have that asset of ignorance. Every day I get to summon my curiosity and courage to ask questions. Good questions.

Good questions gather information to craft a message or plan a project. They challenge assumptions and explore options. They reveal ideas and unlock possibilities.

Some of the best questions are inspired and spontaneous, springing forth from a conversation. “Wow! What motivated you to take that chance?” “Hmm. Who will be involved in getting this done?” “Back up. Why did they make those changes?”

Other questions can be practiced and repeated. Over time, I’ve turned again and again to a handful of dependable questions that work in just about any communication situation. Pulled from my reserve, here are five trusty questions for communicators.

1. What are you really trying to say?

Maybe someone else came up with the words, or maybe you chose them yourself. Either way, this question helps turn a mangled message into something meaningful.

What this question does: Clarifies a complicated message. Finds different words to convey the same idea—or something even better.

When to use this question: When you’ve just heard a long-winded answer or explanation. When you’re staring at a page of complicated corporate speak. When your message includes jargon that is foreign to your target audience.

In context: “I’ve read this message several times, and I’m still confused. Without looking at the page, what are you really trying to say?” or “I hear what you’re saying, but I’m not sure I understand. Can you use different words to tell me what you’re really trying to say?”

2. What do we know about the humans who will receive this message?

Whether you’re communicating internally or externally, business-to-business or business-to-consumer, your target audience is human. You may send a message to thousands of people; but they’ll receive it as individuals. This question helps you think of them that way.

What this question does: Shifts your focus from a mass audience to a single recipient. Puts you in conversation with a living, breathing person who will have a human response to what you say.

When to use this question: When you’re starting a message or campaign. When you’re crafting a message for a specific audience. When you’re “recycling” language for a new purpose.

In context: “What do we know about the humans who will receive this message? Let’s start with the target audience. Who is she? What do we want her to think or believe or do? What turns her on, pisses her off, lights her up, brings her down?” or “Our reviewers and approvers are busy human beings with strong opinions. What matters most to them?”

3. What’s the best thing that could happen?

The purpose of business communication is to get things done. The more clearly you see the desired result, the more prepared you are to achieve it. This question sheds light on the goal.

What this question does: Clarifies the ideal outcome. Helps select words and tone that live up to the expectation. Creates a business case for the message.

When to use this question: When you don’t have a clear sense of the goal. When you need to nail the call to action. When someone is reluctant to communicate.

In context: “Let’s be specific about what we need to accomplish. When people receive this message, what’s the best thing that could happen?” or “You seem reluctant to share this information. If we do communicate, what the best thing that could happen?”

4. What’s the worst thing that could happen?

Risk management belongs as much to communicators as it does to attorneys, actuaries, and compliance officers. This question helps you envision the snares that lie ahead, so you can take steps to avoid them.

What this question does: Prevents hasty decisions. Puts risks in perspective. Anticipates obstacles—so you can decide whether to avoid them or how to overcome them.

When to use this question: When you’re evaluating whether or not to communicate. When you’re working with a risk-averse reviewer, approver, or spokesperson. When you’re preparing contingency plans. When you’re compiling a Q&A document.

In context: “Let’s think about the potential downside of sharing this story. What’s the worst thing that could happen?” or “If this message reaches an unintended audience (such as the press or a competitor), what’s the worst thing that could happen?”

5. What if … ?

Communicating is a creative act. And creativity means challenging assumptions, trying new things, and exploring the unexpected. “What if” questions achieve all this and more.

What this question does: Points to alternatives. Invites new ideas. Draws out possibilities and risks associated with a message (making it a perfect follow-up to questions 3 and 4 above).

When to use this question: When you want to challenge “the way we’ve always done it.” When you’re thinking through a timeline. When you’re brainstorming.

In context: “In the past, we’ve struggled to reach everyone via face-to-face meeting. What if we posted a video instead?” or “What if we push this back a week?” or “What if this goes viral?” or “What if this makes the evening news?” or “What if we replaced all those words with a single photograph?”

* * *

When you ask good questions—whether you’re a wide-eyed newbie or a gray-haired guru—you become known as thoughtful, intelligent, and strategic. That’s the kind of reputation that opens doors, climbs ladders, and builds bridges.